Dimethoxanate

Dimethoxanate (trade names Cothera, Cotrane, Atuss, Perlatoss, Tossizid)^[1] is a cough suppressant of the phenothiazine class.^[2]

Dimethoxanate

Clinical data
Trade names	Atuss, Cothera, Cotrane, Perlatos, Pulmoll, Tussizid
AHFS/Drugs.com	International Drug Names
ATC code	R05DB28 (WHO)
Identifiers
IUPAC name 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate
CAS Number	477-93-0
PubChem CID	10610
ChemSpider	10165 Y
UNII	1E3KG5FWDB
KEGG	D07397 Y
CompTox Dashboard (EPA)	DTXSID50197257
ECHA InfoCard	100.006.838
Chemical and physical data
Formula	C19H22N2O3S
Molar mass	358.46 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OCCOCCN(C)C)N1c3c(Sc2c1cccc2)cccc3
InChI InChI=1S/C19H22N2O3S/c1-20(2)11-12-23-13-14-24-19(22)21-15-7-3-5-9-17(15)25-18-10-6-4-8-16(18)21/h3-10H,11-14H2,1-2H3 Y Key:OOVJCSPCMCAXEX-UHFFFAOYSA-N Y
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Side effects

Dimethoxanate may have analgesic, local anesthetic, and central nervous system depressant effects, but it may also produce nausea and vomiting.^[3]

Pharmacology

It binds to the sigma-1 receptor in the brain with an IC₅₀ of 41 nM.^[4]

Society and culture

Dimethoxanate was introduced in Austria, Belgium, and France in 1911, and in Italy and Spain in 1963.^[5] Approval for marketing in the US was withdrawn by the FDA in 1975 due to lack of evidence of efficacy.^[6]

Synthesis

Synthesis:^[7] Patent:^[8]

Phenothiazine (1) is reacted with phosgene to give Phenothiazine-10-carbonyl chloride [18956-87-1] (2). Further reaction with 2-(2-(dimethylamino)ethoxy)ethanol [1704-62-7] (3) completed the synthesis of Dimethoxanate (4).